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1.
Sci Rep ; 11(1): 17946, 2021 Sep 09.
Artigo em Inglês | MEDLINE | ID: mdl-34504174

RESUMO

Fluorescence imaging of tumours facilitates rapid intraoperative diagnosis. Thus far, a promising activatable fluorescence probe for hepatocellular carcinoma (HCC) has not been developed. Herein, the utility of the fluorescence imaging of HCC using a ß-galactosidase (ß-Gal)-activatable fluorescence probe SPiDER-ßGal was examined. ß-Gal activity was measured in cryopreserved tissues from 68 patients. Live cell imaging of HCC cell lines and imaging of tumour-bearing model mice were performed using SPiDER-ßGal. Furthermore, fluorescence imaging was performed in 27 freshly resected human HCC specimens. In cryopreserved samples, ß-Gal activity was significantly higher in tumour tissues than in non-tumour tissues. Fluorescence was observed in HCC cell lines. In mouse models, tumours displayed stronger fluorescence than normal liver tissue. In freshly resected specimens, fluorescence intensity in the tumour was significantly higher than that in non-tumour liver specimens as early as 2 min after spraying. Receiver operating characteristic curves were generated to determine the diagnostic value of SPiDER-ßGal 10 min after its spraying; an area under the curve of 0.864, sensitivity of 85.2%, and specificity of 74.1% were observed for SPiDER-ßGal. SPiDER-ßGal is useful for the rapid fluorescence imaging of HCC. Fluorescence imaging guided by SPiDER-ßGal would help surgeons detect tumours rapidly and achieve complete liver resection.

2.
Methods Enzymol ; 657: 1-19, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34353483

RESUMO

Photoacoustic (PA) imaging is an emerging imaging modality that combines the advantages of optical imaging and ultrasound imaging. In particular, activatable PA probes, which visualize the presence or the activity of target molecules in terms of a change of the PA signal, are useful tools for functional imaging. In this chapter, we describe the development of small-molecule-based activatable PA probes, focusing on the design and synthesis of PA-MMSiNQ, our recently developed activatable PA probe for HOCl. We also describe the protocols used for evaluation of PA-MMSiNQ with a UV-vis spectrometer and a PA imaging microscope.


Assuntos
Técnicas Fotoacústicas , Imagem Molecular , Imagem Óptica , Análise Espectral
3.
Photodiagnosis Photodyn Ther ; 35: 102420, 2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-34242818

RESUMO

BACKGROUND: Accurate diagnosis of peritoneal metastasis in gastric cancer (GC) is important to determine the appropriate treatment. This study aimed to examine whether matrix metalloprotease-14 (MMP-14) was a candidate enzyme in fluorescence imaging for the diagnosis of peritoneal metastasis in GC. METHODS: GC and normal peritoneal (NP) tissues from 96 and 20 patients, respectively were evaluated for MMP-14 expression. Live cell imaging of GC cell lines (NUGC4, MKN45, MKN74, HGC-27, and Kato-III) was performed using the MMP-14-activatable fluorescence probe; BODIPY-MMP. Furthermore, the overall survival (OS) was calculated in all patients (n = 96). RESULTS: MMP-14 expression was significantly higher in GC tissues (median: 3.57 ng/mg protein; range:0.64-24.4 ng/mg protein) than in NP tissues (median: 1.34 ng/mg protein; median: 0.53-3.09 ng/mg protein) (P < 0.01). Receiver operating characteristic curves showed that the area under the curve, sensitivity, and specificity were 0.907, 84.4%, and 90.0%, respectively. In live cell imaging using the BODIPY-MMP, fluorescence was observed in five GC cell lines. In the analysis of OS, the high expression of the MMP-14 group had a significantly poorer OS rate than the low expression of the MMP-14 group (P = 0.02). In the multivariate analyses, MMP-14 expression was an independent risk factor for OS (hazard ratio: 2.33; 95 % confidence interval: 1.05-5.45; P = 0.04). CONCLUSION: MMP-14 is a promising enzyme in intraoperative fluorescence imaging for peritoneal metastasis in GC, especially in patients with poor prognosis.


Assuntos
Neoplasias Peritoneais , Fotoquimioterapia , Neoplasias Gástricas , Biomarcadores Tumorais , Humanos , Metaloproteinase 14 da Matriz , Neoplasias Peritoneais/diagnóstico por imagem , Fotoquimioterapia/métodos , Fármacos Fotossensibilizantes , Prognóstico , Neoplasias Gástricas/diagnóstico por imagem
4.
Cell Rep ; 36(1): 109311, 2021 Jul 06.
Artigo em Inglês | MEDLINE | ID: mdl-34233188

RESUMO

In this study, we present a live-cell-based fluorometric coupled assay system to identify the compounds that can regulate the targeted metabolic pathways in live cells. The assay is established through targeting specific metabolic pathways and using "input" and "output" metabolite pairs. The changes in the extracellular output that are generated and released into the extracellular media from the input are assessed as the activity of the pathway. The screening for the glycolytic pathway and amino acid metabolism reveals the activities of the present drugs, 6-BIO and regorafenib, that regulate the metabolic fate of tumor cells.

5.
Methods Mol Biol ; 2274: 193-206, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34050473

RESUMO

Fluorescence (FL)-guided detection of cancer is one of the most promising approaches to achieve intraoperative assessment of surgical margins. Enzymes, such as aminopeptidase, carboxypeptidase, and glycosidase, whose activities are increased in cancer, have attracted great interest as imaging targets for rapid and sensitive visualization of cancerous tissues with fluorescent probes. Activatable probes, which are initially nonfluorescent but become strongly fluorescent upon rapid one-step cleavage of their substrate moiety by the target enzyme, are especially promising for practical clinical application during surgical or endoscopic procedures due to the highly amplified FL change generated by enzyme-catalyzed turnover at lesion sites. Here, we describe robust protocols for using activatable fluorescent probes targeting cancer-associated enzyme activities to visualize cultured cancer cells, metastatic cancer in a mouse model, and cancerous lesions in surgical specimens from patients.


Assuntos
Aminopeptidases/metabolismo , Carboxipeptidases/metabolismo , Diagnóstico por Imagem/métodos , Corantes Fluorescentes/química , Neoplasias/patologia , Neoplasias Peritoneais/secundário , Animais , Feminino , Humanos , Masculino , Camundongos Endogâmicos BALB C , Camundongos Nus , Microscopia Confocal , Neoplasias/diagnóstico por imagem , Neoplasias/enzimologia , Neoplasias Peritoneais/diagnóstico por imagem , Neoplasias Peritoneais/enzimologia , Células Tumorais Cultivadas , Ensaios Antitumorais Modelo de Xenoenxerto
6.
Sci Rep ; 11(1): 10664, 2021 05 21.
Artigo em Inglês | MEDLINE | ID: mdl-34021168

RESUMO

Diagnosis of peritoneal metastasis in gastric cancer (GC) is essential for determining appropriate therapeutic strategies and avoiding non-essential laparotomy or gastrectomy. Recently, a variety of activatable fluorescence probes that can detect enzyme activities have been developed for cancer imaging. The aim of this study was to identify the key enzyme involved in peritoneal metastasis in GC. The enzymatic activity of gamma-glutamyl transpeptidase, dipeptidyl peptidase IV, and ß-galactosidase (ß-Gal) was assessed in lysates prepared from preserved human GC (n = 89) and normal peritoneal (NP; n = 20) samples. ß-Gal activity was significantly higher in the human GC samples than in NP samples, whereas no differences were observed in the activities of the other enzymes. Therefore, we used SPiDER-ßGal, a fluorescent probe that can be activated by ß-Gal, for imaging GC cell lines, peritoneal metastasis in a mouse model, and fresh human resected GC samples (n = 13). All cell lines showed fluorescence after applying SPiDER-ßGal, and metastatic nodules in the mice gradually developed high fluorescence that could be visualized with SPiDER-ßGal. The human GC samples showed significantly higher fluorescence than NP samples. ß-Gal is a useful target enzyme for fluorescence imaging of peritoneal metastasis in GC.

7.
Clin Cancer Res ; 27(14): 3936-3947, 2021 Jul 15.
Artigo em Inglês | MEDLINE | ID: mdl-34031057

RESUMO

PURPOSE: Five-aminolevulinic acid (5-ALA) is widely used as an intraoperative fluorescent probe for radical resection of high-grade glioma, and thus aids in extending progression-free survival of patients. However, there exist some cases where 5-ALA fails to fluoresce. In some other cases, it may undergo fluorescence quenching but cannot be orally readministered during surgery. This study aimed to develop a novel hydroxymethyl rhodamine green (HMRG)-based fluorescence labeling system that can be repeatedly administered as a topical spray during surgery for the detection of glioblastoma. EXPERIMENTAL DESIGN: We performed a three-stage probe screening using tumor lysates and fresh tumor tissues with our probe library consisting of a variety of HMRG probes with different dipeptides. We then performed proteome and transcript expression analyses to detect candidate enzymes responsible for cleaving the probe. Moreover, in vitro and ex vivo studies using U87 glioblastoma cell line were conducted to validate the findings. RESULTS: The probe screening identified proline-arginine-HMRG (PR-HMRG) as the optimal probe that distinguished tumors from peritumoral tissues. Proteome analysis identified calpain-1 (CAPN1) to be responsible for cleaving the probe. CAPN1 was highly expressed in tumor tissues which reacted to the PR-HMRG probe. Knockdown of this enzyme suppressed fluorescence intensity in U87 glioblastoma cells. In situ assay using a mouse U87 xenograft model demonstrated marked contrast of fluorescence with the probe between the tumor and peritumoral tissues. CONCLUSIONS: The novel fluorescent probe PR-HMRG is effective in detecting glioblastoma when applied topically. Further investigations are warranted to assess the efficacy and safety of its clinical use.

8.
Chem Commun (Camb) ; 57(47): 5802-5805, 2021 Jun 10.
Artigo em Inglês | MEDLINE | ID: mdl-33999073

RESUMO

We have designed and developed non-fluorescent, cell-permeable photoactivatable fluorophores, photoactivatable SPiDERs (paSPiDERs), which exhibit fluorescence activation upon light irradiation, accompanied by the generation of a quinone methide intermediate that binds covalently to intracellular proteins. The fluorescence signal is durable for 24 hours, resistant to fixation and compatible with immunostaining, and selective cell labeling can be achieved at single-cell resolution.


Assuntos
Corantes Fluorescentes/química , Imagem Óptica , Células A549 , Fluorescência , Corantes Fluorescentes/síntese química , Humanos , Microscopia de Fluorescência , Estrutura Molecular , Processos Fotoquímicos
9.
Chem Commun (Camb) ; 57(48): 5969-5972, 2021 Jun 15.
Artigo em Inglês | MEDLINE | ID: mdl-34027523

RESUMO

Optochemical tools that can modulate the activity of the target protein provide an opportunity for studying and regulating the related biological processes. Here we present a DNA-based nongenetic optochemical tool that can control the dynamics of growth factor signaling. This photo-caged mimicry of growth factor can be a promising tool for elucidating a linkage between the dynamics of signaling and the resulting biological outcomes, as well as for manipulating cellular functions and the fate of living cells.


Assuntos
DNA/metabolismo , Proteínas/metabolismo , Animais , DNA/química , Fenômenos Ópticos , Células PC12 , Proteínas/química , Ratos , Transdução de Sinais , Raios Ultravioleta
10.
Proc Natl Acad Sci U S A ; 118(6)2021 02 09.
Artigo em Inglês | MEDLINE | ID: mdl-33542099

RESUMO

Caenorhabditis elegans is used as a model system to understand the neural basis of behavior, but application of caged compounds to manipulate and monitor the neural activity is hampered by the innate photophobic response of the nematode to short-wavelength light or by the low temporal resolution of photocontrol. Here, we develop boron dipyrromethene (BODIPY)-derived caged compounds that release bioactive phenol derivatives upon illumination in the yellow wavelength range. We show that activation of the transient receptor potential vanilloid 1 (TRPV1) cation channel by spatially targeted optical uncaging of the TRPV1 agonist N-vanillylnonanamide at 580 nm modulates neural activity. Further, neuronal activation by illumination-induced uncaging enables optical control of the behavior of freely moving C. elegans without inducing a photophobic response and without crosstalk between uncaging and simultaneous fluorescence monitoring of neural activity.


Assuntos
Controle Comportamental , Caenorhabditis elegans/fisiologia , Caenorhabditis elegans/efeitos da radiação , Luz , Neurônios/fisiologia , Neurônios/efeitos da radiação , Animais , Fluorescência , Interneurônios/fisiologia , Regiões Promotoras Genéticas/genética , Canais de Cátion TRPV/agonistas , Canais de Cátion TRPV/metabolismo
11.
Anal Chem ; 93(7): 3470-3476, 2021 02 23.
Artigo em Inglês | MEDLINE | ID: mdl-33566568

RESUMO

Basic carboxypeptidases (basic CPs) cleave the C-terminal basic amino acid of peptides, and their activity is upregulated in some types of cancers. Therefore, detecting the activity of basic CPs in living cells would be important not only for studying the physiological functions of these enzymes but also for visualization of cancerous tissues. Here, we report two fluorescein diacetate (FDA)-based activatable fluorescence probes, named 5ArgAF-FDA and 5LysAF-FDA, in which the substrate amino acid arginine or lysine is conjugated to the benzene moiety via an azoformyl linker. In live-cell fluorescence imaging of CPM, one of the seven basic CPs, 5ArgAF-FDA showed a larger intracellular fluorescence increase than did 5LysAF-FDA within a few minutes. This increase was inhibited by coincubation with 2-mercaptomethyl-3-guanidinoethylthiopropanoic acid (MGTA), an inhibitor of basic CPs. When 5ArgAF-FDA was applied to a coculture of two breast cancer cell lines with different CPM activities, the fluorescence increase in individual cells was correlated with the expression level of CPM, suggesting that 5ArgAF-FDA has the ability to distinguish cell lines having different levels of CPM activity, owing to its high intracellular retention. We believe these probes will be useful for imaging cancers with upregulated basic CP activity.


Assuntos
Carboxipeptidases , Peptídeos , Fluorescência , Lisina
12.
Gan To Kagaku Ryoho ; 48(2): 176-180, 2021 Feb.
Artigo em Japonês | MEDLINE | ID: mdl-33597353

RESUMO

In this paper, novel rapid cancer imaging techniques using activatable fluorescent probes are showcased, whose fluorescence characteristics are significantly altered to distinguish between cancer sites, which was developed by using unique probe precision design methods established by the authors. The strategy is to develop probes that target enzymes whose activity has been reported to be enhanced in cancer sites, or to find the most suitable probes from a group of developed probes by screening using actual clinical specimens. Several medical technologies have been developed that enable selective detection of cancer sites within minutes by simply spraying the probes on suspected cancer sites. In addition, it has recently become clear that simultaneous imaging of multiple target enzyme activities can not only visualize the lesion site but also distinguish between malignant and benign lesions. It is highly expected that the day will soon come when surgeons will be able to clearly determine the cancer site to be treated and perform precise endoscopic or open-stomach surgery.


Assuntos
Corantes Fluorescentes , Neoplasias , Humanos , Neoplasias/diagnóstico por imagem , Imagem Óptica
13.
EMBO Rep ; 22(3): e49097, 2021 03 03.
Artigo em Inglês | MEDLINE | ID: mdl-33565245

RESUMO

Parkin promotes cell survival by removing damaged mitochondria via mitophagy. However, although some studies have suggested that Parkin induces cell death, the regulatory mechanism underlying the dual role of Parkin remains unknown. Herein, we report that mitochondrial ubiquitin ligase (MITOL/MARCH5) regulates Parkin-mediated cell death through the FKBP38-dependent dynamic translocation from the mitochondria to the ER during mitophagy. Mechanistically, MITOL mediates ubiquitination of Parkin at lysine 220 residue, which promotes its proteasomal degradation, and thereby fine-tunes mitophagy by controlling the quantity of Parkin. Deletion of MITOL leads to accumulation of the phosphorylated active form of Parkin in the ER, resulting in FKBP38 degradation and enhanced cell death. Thus, we have shown that MITOL blocks Parkin-induced cell death, at least partially, by protecting FKBP38 from Parkin. Our findings unveil the regulation of the dual function of Parkin and provide a novel perspective on the pathogenesis of PD.


Assuntos
Mitofagia , Ubiquitina-Proteína Ligases , Sobrevivência Celular , Células HeLa , Humanos , Ubiquitina-Proteína Ligases/genética , Ubiquitina-Proteína Ligases/metabolismo , Ubiquitinação
14.
FASEB J ; 35(2): e21281, 2021 02.
Artigo em Inglês | MEDLINE | ID: mdl-33484199

RESUMO

Osteoclast bone resorption activity is critically regulated to maintain bone homeostasis. Osteoclasts resorb bone by producing protons and acid hydrolase via lysosomal secretion, however, a detailed mechanism remains elusive. PMEPA1 is a vesicular membrane protein, which binds to the NEDD4 family member of ubiquitin ligases. We have previously reported that Pmepa1 is highly expressed in bone resorbing osteoclasts, and regulates bone resorption. Here, we investigated the mechanism of bone resorption regulated by PMEPA1. Mutant mice lacking NEDD4-binding domains of PMEPA1 displayed enhanced bone volume, and reduced bone resorption activity in comparison with those of WT mice. Analysis with pH-sensitive fluorescence probe revealed that proton secretion from osteoclasts significantly decreased in Pmepa1 mutant osteoclasts. Immunofluorescence analysis revealed that PMEPA1 was colocalized with NEDD4, V0A3, and V0D2 subunits of vacuolar ATPase, which regulate the proton production of osteoclasts. In addition, Nedd4 knockdown reduced bone resorption and proton secretion of osteoclasts. Furthermore, Pmepa1 mutation and Nedd4 knockdown altered the cytoplasmic distribution of components of V-ATPase and expression of autophagy-related proteins, suggesting that lysosomal secretion is affected. Collectively, these findings indicate that PMEPA1 controls proton secretion from osteoclasts via NEDD4 by regulating vesicular trafficking, and NEDD4 is an important regulator of bone resorption.


Assuntos
Reabsorção Óssea/metabolismo , Proteínas de Membrana/metabolismo , Ubiquitina-Proteína Ligases Nedd4/metabolismo , Osteoclastos/metabolismo , Prótons , Animais , Autofagia , Sítios de Ligação , Células Cultivadas , Proteínas de Membrana/química , Proteínas de Membrana/genética , Camundongos , Camundongos Endogâmicos C57BL , Mutação , Ligação Proteica , Transporte Proteico , Vesículas Transportadoras/metabolismo , ATPases Vacuolares Próton-Translocadoras/metabolismo
15.
Bioconjug Chem ; 32(2): 234-238, 2021 02 17.
Artigo em Inglês | MEDLINE | ID: mdl-33502173

RESUMO

Aldehyde dehydrogenase 1 (ALDH1) plays an important role as a stem cell marker. In the field of stem cell biology, a green fluorescent ALDH1 probe has been principally used, but there is a need for more options in probe color. We designed and synthesized two blue fluorescent ALDH1 probes using 8-amino BODIPY and aminomethylbenzaldehyde. These probes can be simultaneously used with other color probes. Here, we demonstrate successful examples of the simultaneous use of these probes with green fluorescent protein.


Assuntos
Família Aldeído Desidrogenase 1/metabolismo , Compostos de Boro/química , Corantes Fluorescentes/química , Aminas/química , Linhagem Celular Tumoral , Humanos
16.
Angew Chem Int Ed Engl ; 60(4): 2125-2129, 2021 01 25.
Artigo em Inglês | MEDLINE | ID: mdl-33096584

RESUMO

γ-Glutamyltranspeptidase (GGT) is overexpressed in several types of cancer. Existing GGT-targeting fluorescence probes can image these cancers, but the fluorescent hydrolysis product leaks from the target cancer cells during prolonged incubation or fixation. Here, we present a functionalized fluorescence probe for GGT, 4-CH2 F-HMDiEtR-gGlu, which is designed to generate an azaquinone methide intermediate during activation by GGT; this intermediate reacts with intracellular nucleophiles to generate a fluorescent adduct that is trapped inside the cells, without loss of the target enzyme activity. Application of the probe to patient-derived xenograft (PDX) mice enabled in vivo cancer imaging for a prolonged period and was also compatible with fixation and immunostaining of the cancer tissue.


Assuntos
Corantes Fluorescentes/química , Neoplasias/diagnóstico por imagem , Imagem Óptica/métodos , gama-Glutamiltransferase/metabolismo , Animais , Xenoenxertos , Humanos , Camundongos , Espectrometria de Fluorescência/métodos
17.
Molecules ; 25(24)2020 Dec 16.
Artigo em Inglês | MEDLINE | ID: mdl-33339370

RESUMO

The use of fluorescent probes in a multitude of applications is still an expanding field. This review covers the recent progress made in small molecular, spirocyclic xanthene-based probes containing different heteroatoms (e.g., oxygen, silicon, carbon) in position 10'. After a short introduction, we will focus on applications like the interaction of probes with enzymes and targeted labeling of organelles and proteins, detection of small molecules, as well as their use in therapeutics or diagnostics and super-resolution microscopy. Furthermore, the last part will summarize recent advances in the synthesis and understanding of their structure-behavior relationship including novel computational approaches.


Assuntos
Corantes Fluorescentes/química , Compostos de Espiro/química , Xantenos/química , Trifosfato de Adenosina/análise , Trifosfato de Adenosina/química , Animais , Humanos , Microscopia de Fluorescência , Neoplasias/diagnóstico , Neoplasias/tratamento farmacológico , Neoplasias/metabolismo , Fármacos Fotossensibilizantes/química , Fármacos Fotossensibilizantes/uso terapêutico , Relação Estrutura-Atividade
18.
Sci Rep ; 10(1): 20125, 2020 11 18.
Artigo em Inglês | MEDLINE | ID: mdl-33208865

RESUMO

Dietary phosphate overload induces chronic kidney disease (CKD), and calciprotein particles (CPPs), a form of nanoparticle comprising calcium phosphate and serum proteins, has been proposed to cause renal toxicity. However, the mechanism of CPP cytotoxicity in renal tubular cells is unknown. Here we show that in renal proximal tubular epithelial HK-2 cells, endocytosed CPPs accumulate in late endosomes/lysosomes (LELs) and increase their luminal pH by ~ 1.0 unit. This results in a decrease in lysosomal hydrolase activity and autophagic flux blockage without lysosomal rupture and reactive oxygen species generation. CPP treatment led to vulnerability to H2O2-induced oxidative stress and plasma membrane injury, probably because of autophagic flux blockage and decreased plasma membrane cholesterol, respectively. CPP-induced disruption of lysosomal homeostasis, autophagy flux and plasma membrane integrity might trigger a vicious cycle, leading to progressive nephron loss.


Assuntos
Nanopartículas Calcificantes/toxicidade , Colesterol/metabolismo , Células Epiteliais/metabolismo , Túbulos Renais Proximais/citologia , Lisossomos/metabolismo , Autofagia/efeitos dos fármacos , Autofagia/fisiologia , Fatores de Transcrição de Zíper de Leucina e Hélice-Alça-Hélix Básicos/metabolismo , Nanopartículas Calcificantes/farmacocinética , Fosfatos de Cálcio/química , Linhagem Celular , Membrana Celular/efeitos dos fármacos , Membrana Celular/metabolismo , Permeabilidade da Membrana Celular/efeitos dos fármacos , Endocitose , Células Epiteliais/efeitos dos fármacos , Células Epiteliais/patologia , Humanos , Concentração de Íons de Hidrogênio , Lisossomos/patologia , Estresse Oxidativo/efeitos dos fármacos , Espécies Reativas de Oxigênio/metabolismo
19.
J Am Chem Soc ; 142(49): 20701-20707, 2020 12 09.
Artigo em Inglês | MEDLINE | ID: mdl-33225696

RESUMO

Raman probes based on alkyne or nitrile tags hold promise for highly multiplexed imaging. However, sensing of enzyme activities with Raman probes is difficult because few mechanisms are available to modulate the vibrational response. Here we present a general strategy to prepare activatable Raman probes that show enhanced Raman signals due to electronic preresonance (EPR) upon reaction with enzymes under physiological conditions. We identified a xanthene derivative bearing a nitrile group at position 9 (9CN-JCP) as a suitable scaffold dye, and synthesized four types of activatable Raman probes, which are targeted to different enzymes (three aminopeptidases and a glycosidase) and tuned to different vibrational frequencies by isotope editing of the nitrile group. We validated the activation of the Raman signals of these probes by the target enzymes and succeeded in simultaneous imaging of the four enzyme activities in live cells. Different cell lines showed different patterns of these enzyme activities.


Assuntos
Aminopeptidases/metabolismo , Glicosídeo Hidrolases/metabolismo , Sondas Moleculares/química , Análise Espectral Raman/métodos , Aminopeptidases/química , Linhagem Celular Tumoral , Glicosídeo Hidrolases/química , Humanos , Marcação por Isótopo , Microscopia de Fluorescência , Nitrilas/química , Especificidade por Substrato
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